diff --git a/workspace/a2a_executor.py b/workspace/a2a_executor.py
index 0c160645..b550a350 100644
--- a/workspace/a2a_executor.py
+++ b/workspace/a2a_executor.py
@@ -247,8 +247,6 @@ class LangGraphA2AExecutor(AgentExecutor):
             task_span.set_attribute(A2A_TASK_ID, context.context_id or "")
             task_span.set_attribute("a2a.input_preview", user_input[:256])
 
-            await set_current_task(self._heartbeat, brief_task(user_input))
-
             # Resolve IDs — the RequestContextBuilder always sets them, but
             # we generate fallbacks for safety (e.g. in unit tests).
             task_id = context.task_id or str(uuid.uuid4())
@@ -257,6 +255,12 @@ class LangGraphA2AExecutor(AgentExecutor):
             updater = TaskUpdater(event_queue, task_id, context_id)
 
             try:
+                # set_current_task INSIDE the try so active_tasks is always
+                # decremented by the finally block even if CancelledError hits
+                # during the heartbeat HTTP push. Moving it outside the try
+                # created a window where cancellation left active_tasks stuck
+                # at 1, permanently blocking queue drain. (#2026)
+                await set_current_task(self._heartbeat, brief_task(user_input))
                 messages = _extract_history(context)
                 if messages:
                     logger.info("A2A execute: injecting %d history messages", len(messages))
diff --git a/workspace/claude_sdk_executor.py b/workspace/claude_sdk_executor.py
index e299af6f..893aafdb 100644
--- a/workspace/claude_sdk_executor.py
+++ b/workspace/claude_sdk_executor.py
@@ -426,14 +426,19 @@ class ClaudeSDKExecutor(AgentExecutor):
         # Keep a clean copy of the user's actual message for the memory record,
         # BEFORE any delegation or memory injection.
         original_input = user_input
-        await set_current_task(self.heartbeat, brief_summary(user_input))
         logger.debug("SDK execute [claude-code]: %s", user_input[:200])
 
         prompt = self._prepare_prompt(user_input)
-        prompt = await self._inject_memories_if_first_turn(prompt)
 
         response_text: str = ""
         try:
+            # set_current_task INSIDE the try so active_tasks is always
+            # decremented by the finally block even if CancelledError hits
+            # during the heartbeat HTTP push. Moving it outside the try
+            # created a narrow window where cancellation left active_tasks
+            # stuck at 1 forever, permanently blocking queue drain. (#2026)
+            await set_current_task(self.heartbeat, brief_summary(user_input))
+            prompt = await self._inject_memories_if_first_turn(prompt)
             for attempt in range(_MAX_RETRIES):
                 options = self._build_options()
                 try:
diff --git a/workspace/cli_executor.py b/workspace/cli_executor.py
index 5be84d9f..ce180f82 100644
--- a/workspace/cli_executor.py
+++ b/workspace/cli_executor.py
@@ -280,9 +280,6 @@ class CLIAgentExecutor(AgentExecutor):
         # delegation or memory injection happens.
         original_input = user_input
 
-        # Show current task on canvas — extract a brief one-line summary
-        await set_current_task(self._heartbeat, brief_summary(user_input))
-
         logger.debug("CLI execute [%s]: %s", self.runtime, user_input[:200])
 
         # Inject delegation results that arrived since last message
@@ -290,13 +287,20 @@ class CLIAgentExecutor(AgentExecutor):
         if delegation_context:
             user_input = f"[Delegation results received while you were idle]\n{delegation_context}\n\n[New message]\n{user_input}"
 
-        # Auto-recall: inject prior memories into every prompt. (The CLI
-        # runtimes don't keep a session, so there's no "first turn" concept.)
-        memories = await recall_memories()
-        if memories:
-            user_input = f"[Prior context from memory]\n{memories}\n\n{user_input}"
-
         try:
+            # set_current_task INSIDE the try so active_tasks is always
+            # decremented by the finally block even if CancelledError hits
+            # during the heartbeat HTTP push. Moving it outside the try
+            # created a window where cancellation left active_tasks stuck
+            # at 1, permanently blocking queue drain. (#2026)
+            await set_current_task(self._heartbeat, brief_summary(user_input))
+
+            # Auto-recall: inject prior memories into every prompt. (The CLI
+            # runtimes don't keep a session, so there's no "first turn" concept.)
+            memories = await recall_memories()
+            if memories:
+                user_input = f"[Prior context from memory]\n{memories}\n\n{user_input}"
+
             await self._run_cli(user_input, event_queue)
         finally:
             await set_current_task(self._heartbeat, "")